The synthesis of anthracycline antitumor antibiotics (adriamycin, daunomycin, etc.) will be investigated using three separate routes. One approach proposes transformation of an anthraquinone derived from protetrone, a fermentation by-product of tetracycline producing microorganisms, into anthracyclinones by electrocyclic ring A formation. The formation of the anthraquinone from islandicin will be attempted as an alternative route. A second approach depends on a short, regiospecific total synthesis of the anthraquinone from available substituted benzoic acids. The third approach proposes to prepare optically active anthracyclinones by a convergent route starting from plumbagin and quinic acid.